Minor C-geranylated flavanones from Paulownia tomentosa fruits with MRSA antibacterial activity

Navrátilová, Alice; Schneiderová, Kristýna; Vesela, Daniela; Hanáková, Zuzana; Fontana, A.; Dall’Acqua, Stefano; Cvačka, Josef; Innocenti, Gabbriella; Novotná, Jana; Urbanová, Marie; Pelletier, Jerry; Čížek, Alois; Žemličková, Helena; Šmejkal, Karel

doi:10.1016/j.phytochem.2013.01.002

Cited by 51 publications

(58 citation statements)

References 32 publications

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“…Generally, the spectra corresponded to the π π* and n π* electronic transitions of the flavanone skeleton. 7) A pair of double doublets at δ H 2.98 (1H, J=17.1, 13.2 Hz, H-3α) and 2.62 (1H, J=17.1, 2.7 Hz, H-3β), as well as a double doublet at δ H 5.14 (1H, J=13.2, 2.7 Hz, H-2β) in the 1 H-NMR spectrum (Table 1) further confirmed the presence of a flavanone skeleton, and it was also verified by the 1 H-1 H correlation spectroscopy (COSY) correlations between H-2 and H-3. Moreover, the key heteronuclear multiple bond connectivity (HMBC) correlations from H-2 and H-8 to C-8a as well testified it.…”

Section: Resultsmentioning

confidence: 99%

Anti-inflammatory Prenylated Flavonoids from Helminthostachys zeylanica

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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1) The rhizomes of H. zeylanica are used in a popular antipyretic and anti-inflammatory Chinese herbal medicine known as "Daodi-Ugon." 1,2) This plant has also been shown to exhibit hepatoprotective activity.3,4) Numerous bioactive flavonoids containing prenyl or geranyl groups have been isolated from the rhizomes of H. zeylanica.2-6) Our current systematic phytochemical investigation of this plant led to the isolation of two new prenylflavonoids, neougonins A (1) and B (2), along with nine known flavonoids (Fig. 1). In addition, compound 1 showed significant inhibition of nitric oxide (NO) production with an IC 50 value of 3.32 µM. We report herein the isolation, structural elucidation and biological evaluation of the isolated compounds. Results and DiscussionThe dried whole plants of H. zeylanica were extracted with 95% EtOH, and the concentrated extract was suspended in water and partitioned with EtOAc. The EtOAc fraction was subjected to repeated column chromatography (MCI CHP 20P, 75-150 µm), and octadecyl silica (ODS)) and semi-preparative HPLC to yield two new prenylated flavonoids, neougonins A (1) and B (2), together with nine known flavonoids.Compound 1 was isolated and purified as a yellow amorphous powder. A molecular ion peak at m/z 424.1887 in the high resolution-electron ionization (HR-EI)-MS indicated a molecular formula of C 25 H 28 O 6 , corresponding to 12 degrees of unsaturation. The IR spectrum of 1 showed the presence of hydroxy (ν max 3407 cm ) and carbonyl (ν max 1637 cm −1 ) groups. The UV spectrum showed a disparate course of spectra with maxima at 230 (sh) nm, 298 (sh) nm. Generally, the spectra corresponded to the π π* and n π* electronic transitions of the flavanone skeleton.

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Section: Resultsmentioning

confidence: 99%

Anti-inflammatory Prenylated Flavonoids from Helminthostachys zeylanica

et al. 2016

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…(5) 5.94 6-Geranyl-4′,5,7-trihydroxy-3′,5′-dimethoxyflavanone (6) 6.44 Mimulone B (7) 23.49 Dihydrotricin (8) 44.92 5,7-Dihydroxy-3′,4′,5′-trimethoxyflavanone (9) >50 (+)-Pinoresinol (10) 35.31 (+)-Dehydrovomifoliol (11) 31.82 Aminoguanidine (positive control)…”

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confidence: 99%

“…1) Previous phytochemical studies of the genus Paulownia have reported the isolation of iridoids, 2,3) lignans, 4) furanoquinones, 5) phenolic glycosides, 6) and flavonoids. 7,8) Recently, geranylated flavonoids isolated from the genus Paulownia have been reported to possess a series of bioactivities including antiviral, 9) antioxidant, 10) antimicrobial, 11) cytotoxic, 12) and anti-cholinesterase activities. 13) However, little information is available on the anti-inflammatory constituents of the P. coreana.…”

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“…In our continuing search for the plant-derived inhibitors of nitric oxide (NO) production, the methanolic extract of P. coreana was found to inhibit the lipopolysaccharide (LPS)-induced NO production in RAW264.7 cells. Subsequent bioassay-guided fractionation of the CH 2 Cl 2 -soluble fraction led to the isolation of a new geranylated flavanone, 3′-O-methyl-5′-hydroxydiplacol (1), together with 10 known compounds (2)(3)(4)(5)(6)(7)(8)(9)(10)(11). The structures of known isolates were elucidated on the basis of their spectroscopic analysis ( 1 H-, 13 C-NMR, and electrospray ionization (ESI)-MS) by comparison with those of published data.…”

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Geranylated Flavanones from Paulownia coreana and Their Inhibitory Effects on Nitric Oxide Production

Jin

Lee

et al. 2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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The activity-guided fractionation of the MeOH extract of the flower of Paulownia coreana led to the isolation of a new geranylated flavanone, 3′-O-methyl-5′-hydroxydiplacol (1), along with 10 known compounds (2-11). Their structures were determined using spectroscopic techniques, which included one and two dimensional (1-and 2D)-NMR. Among the isolates, compounds 1-6 showed potent inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide production with IC 50 values ranging 1.48 to 16.66 µM.

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“…with anti-viral, anti-bacterial, and anti-asthmatic activity. [4][5][6][7] We found that a methanolic extract of P. tomentosa flowers was active against EV71, while no activity was detected against CAV16. An activity-directed isolation led to the identification of apigenin as an active component of P. tomentosa antiviral activity.…”

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Antiviral Activity of Paulownia tomentosa against Enterovirus 71 of Hand, Foot, and Mouth Disease

Chen

et al. 2015

Biological ^|^ Pharmaceutical Bulletin

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The bark, leaves, and flowers of Paulownia trees have been used in traditional Chinese medicine to treat infectious and inflammatory diseases. We investigated the antiviral effects of Paulownia tomentosa flowers, an herbal medicine used in some provinces of P. R. China for the treatment of skin rashes and blisters. Dried flowers of P. tomentosa were extracted with methanol and tested for antiviral activity against enterovirus 71 (EV71) and coxsackievirus A16 (CAV16), the predominant etiologic agents of hand, foot, and mouth disease in P. R. China. The extract inhibited EV71 infection, although no effect was detected against CAV16 infection. Bioactivity-guided fractionation was performed to identify apigenin as an active component of the flowers. The EC 50 value for apigenin to block EV71 infection was 11.0 µM, with a selectivity index of approximately 9.3. Although it is a common dietary flavonoid, only apigenin, and not similar compounds like naringenin and quercetin, were active against EV71 infection. As an RNA virus, the genome of EV71 has an internal ribosome entry site that interacts with heterogeneous nuclear ribonucleoproteins (hnRNPs) and regulates viral translation. Cross-linking followed by immunoprecipitation and reverse transcription-polymerase chain reaction (RT-PCR) analysis showed that EV71 RNA was associated with hnRNPs A1 and A2. Apigenin treatment disrupted this association, indicating that apigenin suppressed EV71 replication through a novel mechanism by targeting the trans-acting factors. This study therefore validates the effects of Paulownia against EV71 infection. It also yielded mechanistic insights on apigenin as an active compound for the antiviral activity of P. tomentosa against EV71 infection.

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Minor C-geranylated flavanones from Paulownia tomentosa fruits with MRSA antibacterial activity

Cited by 51 publications

References 32 publications

Anti-inflammatory Prenylated Flavonoids from <i>Helminthostachys zeylanica</i>

Anti-inflammatory Prenylated Flavonoids from <i>Helminthostachys zeylanica</i>

Geranylated Flavanones from <i>Paulownia coreana</i> and Their Inhibitory Effects on Nitric Oxide Production

Antiviral Activity of Paulownia tomentosa against Enterovirus 71 of Hand, Foot, and Mouth Disease

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